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A true mid-century time capsule, 17 Chamberlain Hill Road is a rare opportunity to own a piece of Red Hook history. Built in 1956, this thoughtfully preserved ranch has been held by the same owner since its completion and retains the details that make its era so enduring: original redwood paneling, warm oak floors, birch cabinetry, and western-facing windows that welcome the afternoon light. Set on .69 acres along a private dead-end road, the property has a quiet, established feel. Its history is closely tied to the Red Hook community, where the original owners spent decades, including years teaching in the Red Hook School District. The grounds are just as special, with thoughtfully established plantings that bring color and interest throughout the seasons. A kousa dogwood welcomes you at the driveway, with a redbud, flowering crabapple, and weigela adding to the landscape. In the backyard, a large pink azalea, an impressive hydrangea, and established perennial gardens create a lovely setting to enjoy the outdoors. Inside, the original materials and thoughtful details speak to a different era, when craftsmanship and simplicity went hand in hand. A partially finished lower level offers additional flexible space, along with a workshop for projects, hobbies, or creative pursuits. Just minutes from the vibrant Village of Red Hook, with its local shops, restaurants, and everyday conveniences, this home offers a wonderful balance of privacy and proximity to town. For those who appreciate authentic 1950s character, this is a special find. With its original details and distinctive history, 17 Chamberlain Hill Road offers the opportunity to make a home with character your own.

Highlights

  • Residential
  • Single Family Residence
  • Built in 1956
  • 0.69 Acre Lot
  • 1 Car Garage
  • 11 days on Market

  • Bedrooms
    3
  • Bathrooms
    1
  • Year Built
    1956
  • Architectural Style
    Ranch
  • Construction Materials
    Frame, Vinyl Siding
  • Garage Spaces
    1.0
  • Parking Features
    Driveway, Garage
  • Living Area
    2063.0
  • Interior Features
    Eat-in Kitchen, Storage, Natural Woodwork
  • Appliances
    Microwave, Refrigerator, Washer, Water Softener Owned, Electric Oven, Electric Cooktop
  • Flooring
    Hardwood, Carpet, Linoleum
  • Exterior Features
    Awning(s), Garden
  • Patio And Porch
    Deck
  • Cooling
    Central Air
  • Heating
    Baseboard, Hot Water, Oil
  • Basement
    Full, Partially Finished, Storage Space

  • Acres
    0.69
  • Lot Features
    Level, Private, Garden, Landscaped, Back Yard, Front Yard
  • View
    Trees/Woods, Neighborhood
  • Utilities
    Cable Connected, Electricity Connected, Sewer Connected, Water Connected, Phone Connected
  • Water
    Public, Private, Well

  • County
    Dutchess
  • City
    Red Hook
  • Zip Code
    12571
  • High School
    Red Hook Senior High School
  • Middle School
    Linden Avenue Middle School
  • Elementary School
    Mill Road-Primary Grades

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Frequently Asked Questions

How do I schedule a tour of 17 Chamberlain Hill Rd?

We can make that happen quickly. Click Tour This Home and we'll connect you directly with our vetted local partner to schedule your visit to 17 Chamberlain Hill Rd.

They know residentials in the area well and can give you the guidance you need to buy with confidence.

How do I get more information about 17 Chamberlain Hill Rd?

Click Ask a Question to talk with our team. You already know it is a 3 bed, 1 bath, listed for $549,000. We can talk through recent upgrades, potential seller motivation, how this single family residence compares to others in Red Hook, and can even get you in to see the property quickly.

How do I get a virtual tour of 17 Chamberlain Hill Rd?

Yes! A virtual tour is available for 17 Chamberlain Hill Rd. Click here to view the full walkthrough and explore every room at your own pace. If you would like a guided virtual showing or have questions along the way, we can connect you with our local expert to walk you through it live.

How much is the monthly mortgage payment for 17 Chamberlain Hill Rd?

With a 20% down payment and a 30-year fixed loan at an illustrative 7.25% rate, the ez Mortgage Calculator estimates the monthly payment for 17 Chamberlain Hill Rd at around $3,736. This includes estimated property taxes and insurance.

Want to see how this changes with different down payments or interest rates? Jump to the calculator to run the numbers and fine-tune your plan.

How do I get pre-approved to buy 17 Chamberlain Hill Rd?

Stand out in a competitive market by getting pre-approved today. Our quick and private pre-approval process helps you understand your true buying power—no credit pull required to explore all of your options.

Or, let us connect you with our preferred local lender in Dutchess County. They will give you all of your available financing options, based on your specific situation and what is available to you.

Can I negotiate the asking price for 17 Chamberlain Hill Rd?

In most cases, yes. Whether 17 Chamberlain Hill Rd is priced competitively or not, your best offer depends on your personal situation, the seller's timeline, and recent activity in Red Hook's market. Our preferred local partner will help you craft a strategy—factoring in comparable properties that have sold, timing, and deal structure—to make a smart, strong offer. Click here to ask about negotiation opportunities.

How do I make an offer on 17 Chamberlain Hill Rd?

We can handle that for you. Our preferred local agent specializes in residentials in Red Hook and can guide you through every step of the offer process.

You need an expert who is looking out for your best interests. From market valuation to contingencies and timing, they'll help you present a compelling offer that fits your goals. Click Ask a Question to get started today.

What is the price per square foot for this home?

This home is listed at $549,000 with 2,063 sqft of space—that comes out to approximately $266 per square foot.

How long has this property been on the market?

17 Chamberlain Hill Rd was listed on November 02, 2026, which means it's been on the market for 11 days.

Want to keep tabs on it? Click the ♥ to favorite this home and get notified of price drops or changes.

When was this house built?

This home was built in 1956, making it approximately 70 years old.

What is the lot size of this property?

17 Chamberlain Hill Rd sits on a 0.69-acre lot, which is 30,056 square feet.

What schools are assigned to this property?

Based on MLS info, this home is zoned for:

  • Elementary: Mill Road-Primary Grades
  • Middle: Linden Avenue Middle School
  • High: Red Hook Senior High School

Want to see how these schools compare? Check out our Dutchess County School Guide to see ratings, reviews, and more for the schools in the area.

What are the property taxes for 17 Chamberlain Hill Rd?

The most recent public record shows annual property taxes for 17 Chamberlain Hill Rd were approximately $7,347. This may change with reassessment or exemptions. Our local partner can verify current tax amounts and help you estimate future costs based on your situation.

Is 17 Chamberlain Hill Rd still available for sale?

Yes, this home is still available! Click the ♥ to favorite it so you don't miss any changes—or ask our local expert to schedule a time to see it in person.

Source: ez Home Search, MLS Data

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Listing information provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed by the MLS. The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed. Copyright 2026, OneKey MLS. All rights reserved.

Last Updated: November 13, 2026 at 04:56PM | Source: OneKey MLS | MLS#: 1068227